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【结 构 式】 
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【分子编号】24560 【品名】3-Bromophthalide; 3-Bromo-2-benzofuran-1(3H)-one 【CA登记号】6940-49-4 |
【 分 子 式 】C8H5BrO2 【 分 子 量 】213.0305 【元素组成】C 45.11% H 2.37% Br 37.51% O 15.02% |
合成路线1
该中间体在本合成路线中的序号：(A)This compound can be obtained in tvvo different ways: 1) The reaction of 3-bromophthalide (A) with 5-methoxy-2-methyl-1H-indole-3-acetic acid (I) previously salified with triethylamine in refluxing acetone gives (±)-1,3-dihydro-3-oxo-1-isobenzofuranyl-5-methoxy-2-methyl-1H-indole-3-acetate (II). Compound (II) is salified with sodium hydride and then acylated with p-chlorobenzoyl chloride (B). 2) By condensation of the organic salt of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid (III) with 3-bromophthalide (A).
| 【1】 AR 282717 . |
| 【2】 Torriani, H.; Talmetacin. Drugs Fut 1982, 7, 11, 825. |
| 【3】 Los, M.A.; BE 0858897 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10295 | p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride | 122-01-0 | C7H4Cl2O | 详情 | 详情 |
| (A) | 24560 | 3-Bromophthalide; 3-Bromo-2-benzofuran-1(3H)-one | 6940-49-4 | C8H5BrO2 | 详情 | 详情 |
| (I) | 37079 | 5-Methoxy-2-methyl-1H-indole-3-acetic acid; 2-(5-Methoxy-2-methyl-1H-indol-3-yl)acetic acid | 2882-15-7 | C12H13NO3 | 详情 | 详情 |
| (II) | 37080 | 3-oxo-1,3-dihydro-2-benzofuran-1-yl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate | C20H17NO5 | 详情 | 详情 | |
| (III) | 22930 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid | C19H16ClNO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Two different ways to obtain talniflumate were developed: The first method is by reacting the previously salified niflumic acid (II) with 3-bromophthalide (I). The second way is by condensation of salified 2-halonicotinic acid (III) with 3-bromophthalide (I) to give the corresponding phthalidyl ester (IV), which is then treated with 3-trifluoromethylaniline (V).
| 【1】 Boned, J.; Los, M.; Piccinali, C.; Acidos anilino nicotinico y N-arilantranilicos convenientemente sustituidos. VII Latinoamerican Congress Pharmacology 1978. |
| 【2】 GB 381578 . |
| 【3】 US 879749 . |
| 【4】 Procedimiento para la obtencion de nuevos esterees de acidos fenil- y piridin-3-carboxilicos sustituidos. ES 474566 . |
| 【5】 Phthalidyl 2-(3'-trifluoromethylanilino)pyridine-3-caboxylalate and process for its preparation. AR 209858; GB 1553171 . |
| 【6】 Nouveaux esters d'acides phényl- et pyridine-3-carboxylique et procédé premettant leur préparation. BE 0858864 . |
| 【7】 Torriani, H.; Talniflumate. Drugs Fut 1979, 4, 6, 448. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 24560 | 3-Bromophthalide; 3-Bromo-2-benzofuran-1(3H)-one | 6940-49-4 | C8H5BrO2 | 详情 | 详情 |
| (II) | 33257 | sodium 2-[3-(trifluoromethyl)anilino]nicotinate | C13H8F3N2NaO2 | 详情 | 详情 | |
| (III) | 33255 | sodium 2-chloronicotinate | C6H3ClNNaO2 | 详情 | 详情 | |
| (IV) | 33256 | 3-oxo-1,3-dihydro-2-benzofuran-1-yl 2-chloronicotinate | C14H8ClNO4 | 详情 | 详情 | |
| (V) | 26347 | 3-(trifluoromethyl)phenylamine; 3-(trifluoromethyl)aniline; 3-aminobenzotrifluoride | 98-16-8 | C7H6F3N | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(IV)1) The reaction of 3-bromophthalide with 2-hydroxybenzoic acid (I), previously salified with triethylamine in refluxing acetone gives 1,3-dihydro-3-oxo-1-isobenzofuranyl 2-hydroxybenzoate (II). Compound (II) is acetylated with acetic anhydride, using sulfuric acid as catalizer.
| 【1】 (Laboratorios Bagó); Nouveaux esters de l'acide benzoique substitue. BE 0884978 . |
| 【2】 Castaner, J.; Prous, J.; Talosalate. Drugs Fut 1986, 11, 5, 394. |
合成路线4
该中间体在本合成路线中的序号：(IV)2) By condensation of an organic salt of 2-acetyloxybenzoic acid (III) with 3-bromophthalide.
| 【1】 Los, M.A. (Laboratorios Bagó); Methods of treating mammals suffering from inflammation and pain. BE 0858864; JP 8162049; US 4256760 . |
| 【2】 Castaner, J.; Prous, J.; Talosalate. Drugs Fut 1986, 11, 5, 394. |